Cornforth reagent → (E)-2-tridecen-4,7-diyn-1-al

Pyridinium dichromate (60 g) was stirred with dichloromethane (250 mL) at 0° and treated over a period of 5 min with a solution of (E)-2-tridecen-4,7-diyn-1-ol (20 g) dissolved in dichloromethane. The cooling bath was then removed and the reaction mixture was stirred for a further 3 hours (slight exotherm; maximum temperature 33°-35°). Ether (250 mL) was then added and the solids were filtered off (through paper) and washed with more ether. The combined filtrates were concentrated and the residue was treated with hexane and filtered through celite. The filtrate was then washed with water (5×250 mL), dried (MgSO4) and concentrated to a small volume (100 ml). This solution was purified by liquid chromatography (two columns, 4:1 parts by volume hexane-ethyl acetate) to give the pure (E)-2-tridecen-4,7-diyn-1-al (11 g).

1. customThe cooling bath was then removed
2. additionEther (250 mL) was then added
3. filtrationthe solids were filtered off (through paper)
4. washwashed with more ether
5. concentrationThe combined filtrates were concentrated
6. additionthe residue was treated with hexane
7. filtrationfiltered through celite
8. washThe filtrate was then washed with water (5×250 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated to a small volume (100 ml)
11. customThis solution was purified by liquid chromatography (two columns, 4:1 parts by volume hexane-ethyl acetate)

ORD record

ord-2cfa2acad0aa45babe9c2f24a1d062d5

Source dataset

uspto-grants-1982_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04311645